Heterogeneity of the interflavanyl bond in proanthocyanidins from natural sources lacking C-4(C-ring)deoxy flavonoid nucleophiles
Heterogeneity of the interflavanyl bond in proanthocyanidins from natural sources lacking C-4(C-ring)deoxy flavonoid nucleophiles
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DOI：
10.1016/j.phytochem.2005.01.014
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发表时间：
2005-09-01
期刊：
影响因子：
3.8
通讯作者：
Slade, D
中科院分区：
文献类型：
--
作者：
Ferreira, D;Marais, JPJ;Slade, D
植物界中的原花色素池通常涉及主要连接黄烷-3-醇组成部分的碳-碳键的存在。黄烷-3-醇单元的这样的整体经由衍生自黄烷-4-醇和/或黄烷-3，4-二醇的黄烷-4-基碳阳离子（或它们的等价物）的亲电芳族取代和黄烷-3-醇亲核试剂的m-氧化的A-环的亲核中心而产生。在缺乏这些有效的黄烷-3-醇亲核试剂与其形成碳-碳键的能力的情况下，替代中心作为黄烷酰键形成的参与者出现。这种现象在几种南半球心材物种中的各种原矢车菊苷肽、原刺槐苷肽、原芸香苷肽、原黑素苷肽和原teracacinidin型原花色素和无色花色素的分布中得到了证实。(c)2005爱思唯尔有限公司保留所有权利。
The proanthocyanidin pool in the floral kingdom usually involves the presence of carbon-carbon bonds linking predominantly flavan-3-ol constituent moieties. Such an ensemble of flavan-3-ol units originates via electrophilic aromatic substitution of flavan-4-yl carbocations (or their equivalents) derived from flavan-4-ols and/or flavan-3,4-diols and the nucleophilic centers of the m-oxygenated A-rings of flavan-3-ol nucleophiles. In the absence of these potent flavan-3-ol nucleophiles with their aptitude for the formation of carbon-carbon bonds, alternative centers emerge as participants in interflavanyl bond formation. Such a phenomenon is demonstrated for the distribution of various profisetinidin-, prorobinetinidin-, proguibourtinidin-, promelacacinidin- and proteracacinidin-type pro- and leuco-anthocyanidins in several southern hemisphere heartwood species. (c) 2005 Elsevier Ltd. All rights reserved.